However, you can likely sell all the properties in the required timeline to do the 1031k, although that will take some effort/cooperation between multiple buyers/brokers, considering the separate markets.  

I could be wrong but I thought I saw that Sacramento requires primary residence for the owner for STR.Do you live in Sacramento or nearby ?

Real estate investing requires a good deal of research, so build your arsenal and over time you'll be an old pro. 

I am also looking for tax optimization as the business will require cash reserves and is a high risk business from a liability perspective.

Ask your lender about their recast requirements (payment amount and frequency).

That is a big move, and I wish you all the best @Maxwell Silva on your journey.In terms of a BIO, I would absolutely use your experience in the healthcare field as no doubt you probably contain the following skills:Patience - Working at the level the client requires (whether first time home buyer or experienced investor)Detail Oriented - Ensuring that every important detail is accounted forPeople Person - Putting the needs of others firstGood team player - Good at coordinating and working with a team (title co, lender, other Realtors, etc)Dedicated - Committed to meeting deadlines, and helping people accomplish their RE goalsThese should get you started. 

.- The 203(k) will allow you to bid on properties that need repairs that won't qualify for a traditional mortgage => less competition => better purchase price.You will need to find a great local contractor you can trust to supply the required bids to qualify for the 203(k).- After closing, you can do some of the work yourself to save money, but the program doesn't allow you to pay yourself.You will want to buy a Class B property, maybe Class C+, in an area that seems to be improving.

Helps with your debt to income, better opportunities at cash flow, and typically requires less down to purchase.In regards to challenges, I usually build in an extra 10-15% to deal with things that I can't see behind the walls, including dry rot, electrical or plumbing issues, etc.

"I think we all agree that being fully transparent is beneficial to real estate investing"....Let's try LEGALLY REQUIRED. 

Scaling up properties requires cash flow or equity, continuous education, networking, mentorship, patience, and persistence.